Sulfur ylides 13. Synthesis and intramolecular cyclization of keto-stabilized sulfur ylides |
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Authors: | F. Z. Galin I. M. Sakhautdinov S. N. Lakeev V. A. Egorov A. A. Fatykhov I. O. Maidanova |
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Affiliation: | (1) Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054 Ufa, Russian Federation |
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Abstract: | Keto-stabilized sulfur mono-and bisylides were obtained from N-phthalylglutamic acid and their intramolecular cyclization was studied. The intramolecular cyclization of the ylide obtained at the α-carboxy group gave a product of the pyrrolizidinedione structure; bisylide yielded a cycloheptene derivative as the result of intramolecular recombination of intermediate dicarbene. The ylide obtained at the γ-carboxy group underwent no cyclization, giving methylthio ketone and oxo benzoate. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2771–2776, December, 2005. |
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Keywords: | N-phthalylglutamic acid keto-stabilized sulfonium ylide intramolecular cyclization intramolecular recombination of dicarbene |
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